Zinc-mediated ring-expansion and chain-extension reactions of β-keto esters

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 8245-8247

  Xue, Song ^a   Liu, Yong Kang ^a   Li, Le Zhen ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BETA KETOESTER DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL STRUCTURE; QUANTUM YIELD; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

ESTERS; INDICATORS AND REAGENTS; KETONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ZINC;

EID: 25444444797     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0512498     Document Type: Article

References (32)

1. (a) Wender, P. A.; Lechleiter, J. C. J. Am. Chem. Soc. 1980, 102, 6340.
2. (b) Gibbons, E. G. J. Am. Chem. Soc. 1982, 104, 1767.
3. (c) Kato, N.; Kataoka, H.; Ohbuchi, S.; Tahaka, S.; Takeshita, H. J. Chem. Soc., Chem. Commun. 1988, 354.
4. (d) Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizaden, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, D. D.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597.
5. Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991.
6. (a) Dowd, P.; Choi, S. C. J. Am. Chem. Soc. 1987, 109, 3493.
7. (b) Dowd, P.; Choi, S. C. J. Am. Chem. Soc. 1987, 109, 6548.
8. (c) Dowd, P.; Choi, S. C.; Tetrahedron 1989, 45, 77.
9. (d) Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
10. (e) Yet, L. Tetrahedron 1999,55, 9349.
11. (f) Baldwin, J. E.; Adlington, R. M.; Robertson, J. J. Chem. Soc., Chem. Commun. 1988, 1404.
12. (g) Baldwin, J. E.; Adlington, R. M.; Robertson, J. Tetrahedron 1989, 45, 909.
13. (a) Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216.
14. (b) Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. Tetrahedron 1998, 54, 2347.
15. (c) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
16. Sugi, M.; Sakuma, D.; Togo, H. J. Org. Chem. 2003, 68, 7629.
17. Brogan, J. B.; Zercher, C. K. J. Org. Chem. 1997, 62, 6444.
18. (a) Ronsheim, M. D.; Hilgenkamp, R.; Zercher, C. K. Org. Synth. 2002, 79, 146.
19. (b) Lai, S.; Zercher, C. K.; Jasinski, J. P.; Reid, S. N.; Staples, R. J. Org. Lett. 2001, 3, 4169.
20. (c) Hilgenkamp, R.; Zercher, C. K. Org. Lett. 2001, 3, 3037.
21. (d) Ronsheim, M. D.; Zercher, C. K. J. Org. Chem. 2003, 68, 4535.
22. Hilgenkamp, R.; Zercher, C. K. Tetrahedron 2001, 57, 8793.
23. Verbicky, C. A.; Zercher, C. K. J. Org. Chem. 2000, 65, 5615.
24. (a) Xue, S.; Li, Y. L.; Han, K. Z.; Yin, W.; Wang, M.; Guo, Q. X. Org. Lett. 2002, 4, 905.
25. (b) Xue, S.; He, L.; Han, K. Z.; Liu, Y. K.; Guo, Q. X. Synlett. 2005, 8, 1247.
26. (a) Yang, Z.; Lorenz, J. C.; Shi, Y. Tetrahedron Lett. 1998, 39, 8621.
27. (b) Lorenz, J. C.; Long, J.; Yang, Z. Q.; Xue, S.; Xie, Y. N.; Shi, Y. J. Org. Chem. 2004, 69, 327.
28. (a) Carter, K. N.; Taverner, T.; Schiesser, C. H.; Greenberg, M. M. J. Org. Chem. 2000, 65, 8375.
29. (b) Evans, D. A.; Burch, J. D. Org. Lett. 2001, 3, 503.
30. (c) Carpita, A.; Ribecai, A.; Rossi, R.; Stabile, P. Tetrahedron 2002, 58, 3673.
31. (d) Charette, A. B.; Lacasse, M.-C. Org. Lett. 2002, 4, 3351.
32. 2I (9 mmol) with 5-ethoxycarbonyl-1,2-benzo-2-oxocyclohexenone 1 (650 mg, 3 mmol) gave the desired product 2 in comparable yield (562 mg, 81%) under the same procedure. See the Supporting Information for details.